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. 2018 Oct 19;3(10):13647–13666. doi: 10.1021/acsomega.8b01481

Scheme 5. Synthesis of (2S)-2-Cyanopyrrolidine p-Toluenesulfonate 29 and (2R)-2-Methylpyrrolidine Hydrochloride 33.

Scheme 5

Reagents and conditions: (a) (1) ClCO2Et, Et3N, THF, −25 °C; (2) aq. NH3, THF, −25 °C, 86%; (b) POCl3, imidazole, pyridine, 0 °C to rt, 90%; (c) (1) TFA, anisole, 0 °C; (2) p-TsOH·H2O, quant; (d) BH3-THF complex, THF, 0 °C, 98%; (e) MsCl, Et3N, THF, 0 °C, 95%; (f) NaBH4, DMSO, 80 °C, 46%; and (g) HCl in 1,4-dioxane, rt, quant.